Tetrahedron p. 3715 - 3722 (1986)
Update date:2022-07-31
Topics:
Farina, Francisco
Maestro, M. Carmen
Martin, M. Rosario
Martin, M. Victoria
Sanchez, Felix
Soria, M. Luisa
The reactions of 3-bromo-5-methoxyfuran-2(5H)-one (1) with nucleophiles in acetonitrile, in the presence of potassium carbonate and tetrabutylammonium bromide as a catalyst, are reported.The bromofuranone 1 reacts with several carbon and oxygen nucleophiles to give the cyclopropane bis-lactones 7, 8, 11 or 12.When 1 is reacted with diethylamine or propane-2-thiol in a 2:1 ratio, similar cyclopropane bis-lactones 16 or 21, respectively, are formed.This behaviour is explained on the basis of a mechanism involving a double Michael addition, followed by ring closure via internal nucleophilic substitution of the halogen.
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